p-Toluenesulfonic acid → 2,3:5,6-Di-O-isopropylidene-L-gulonolactone

HRID 329967

反応式

HRID 329967 の反応式
[CH2:1]([OH:12])[C@H:2]([OH:11])[C@H:3]1[O:8][C:6](=[O:7])[C@@H:5]([OH:9])[C@H:4]1[OH:10].CO[C:15](OC)([CH3:17])[CH3:16].[C:20]1(C)[CH:25]=CC(S(O)(=O)=O)=C[CH:21]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CC(C)=O.C(OCC)(=O)C>[CH3:16][C:15]1([CH3:17])[O:11][CH:2]([CH:3]2[O:8][C:6](=[O:7])[CH:5]3[O:9][C:20]([CH3:25])([CH3:21])[O:10][CH:4]23)[CH2:1][O:12]1

参加物

8

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 439373L-Gulonic acid, gamma-lactone2 回HCID 516892Sodium Bicarbonate

生成物 1

HCID 5682882,3:5,6-Di-O-isopropylidene-L-gulonolactone収率 85%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

m.p. 155° C. (from ethyl acetate) [α]D20 -76.6° (c, 1.99 in CHCl3), was prepared from L-gulonolactone in 85% yield as previously described by Fleet in copending application Ser. No. 249,153, filed Sept. 26, 1988. According to this method, the title compound is synthesized by treatment of L-gulonolactone with acetone and 2,2-dimethoxypropane and a catalytic amount of p-toluenesulfonic acid under dry nitrogen for 36 hours (h) followed by stirring with an excess of sodium bicarbonate, removing the solvent under reduced pressure, dissolving the residue in dichloromethane, washing with water, drying the organic extracts (MgSO4), removing the solvent under reduced pressure and recrystallizing from ethyl acetate to give a white crystalline solid.

後処理

  1. customremoving the solvent under reduced pressure
  2. dissolutiondissolving the residue in dichloromethane
  3. washwashing with water
  4. dry with materialdrying the organic extracts (MgSO4)
  5. customremoving the solvent under reduced pressure
  6. customrecrystallizing from ethyl acetate
  7. customto give a white crystalline solid

出典と根拠

ORDレコード
ord-bdbb1b62a75e4e439207e4069eb2d41a
出典データセット
uspto-grants-1990_01
特許番号
US04894388

関連ノート

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